4-cyclohexylidene-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-butene | 339167-12-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 4-cyclohexylidene-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-butene
• 英文别名: 2-(1-Cyclohexylidenebut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-(1-cyclohexylidenebut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 339167-12-3
• 化学式: C₁₆H₂₇BO₂
• 分子量: 262.2
• InChiKey: QWIAXFKRRUDNIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘苯 、 4-cyclohexylidene-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-butene 在 四(三苯基膦)钯 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以15 mg的产率得到4-cyclohexylidene-4-phenyl-1-butene
  参考文献：
  名称：

  Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons

  摘要：

  A novel and efficient method for gem-dimetalation of carbenoids has been demonstrated. Treatment of alkylidene-type lithium carbenoids with such an interelement compound as silylborane or diboron to generate the corresponding borate complex, followed by warming to room temperature, induced migration of the silyl or boryl group from a negatively charged boron atom to the carbenoid carbon to afford 1-boryl-1-silyl-1-alkenes or 1,1-diboryl-1-alkenes in good yields. Carbon-carbon bond forming transformations of the gem-dimetalated compounds mediated by boron or silicon is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00648-8
• 作为产物：
  描述：

  (1,1-dibromomethylene)cyclohexane 在 四(三苯基膦)钯 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 为溶剂， 反应 12.17h， 生成 4-cyclohexylidene-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-butene
  参考文献：
  名称：

  Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons

  摘要：

  A novel and efficient method for gem-dimetalation of carbenoids has been demonstrated. Treatment of alkylidene-type lithium carbenoids with such an interelement compound as silylborane or diboron to generate the corresponding borate complex, followed by warming to room temperature, induced migration of the silyl or boryl group from a negatively charged boron atom to the carbenoid carbon to afford 1-boryl-1-silyl-1-alkenes or 1,1-diboryl-1-alkenes in good yields. Carbon-carbon bond forming transformations of the gem-dimetalated compounds mediated by boron or silicon is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00648-8

文献信息

• Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons
  作者：Takuya Kurahashi、Takeshi Hata、Hirokazu Masai、Hirotaka Kitagawa、Masaki Shimizu、Tamejiro Hiyama

  DOI：10.1016/s0040-4020(02)00648-8

  日期：2002.8

  A novel and efficient method for gem-dimetalation of carbenoids has been demonstrated. Treatment of alkylidene-type lithium carbenoids with such an interelement compound as silylborane or diboron to generate the corresponding borate complex, followed by warming to room temperature, induced migration of the silyl or boryl group from a negatively charged boron atom to the carbenoid carbon to afford 1-boryl-1-silyl-1-alkenes or 1,1-diboryl-1-alkenes in good yields. Carbon-carbon bond forming transformations of the gem-dimetalated compounds mediated by boron or silicon is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.